Isobutyric Acid → HCID 19047496, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of lithium diisopropylamide (prepared from 4.8 g, (47.8 mmol) of diisopropylamine and 19.1 ml, (2.5M, 47.8 mmol) of n-BuLi) in 50 ml of THF was added isobutyric acid (2.2 ml, 23.9 mmol) at 0° C. and the mixture was allowed to warm to 45° C. with stirring. To the mixture cooled to -78° C., was added 4.3 g (23.9 mmol) of HMPA followed by a solution of 1-octyl bromoacetate (6 g, 23.9 mmol) in 50 ml of THF under argon at -78° C. The mixture was quenched with 1N HCl, warmed to room temperature, and extracted with ether (3×50ml). The organic layer was dried over magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (10% methanol/ethyl acetate) to afford 0.8 g of 3-(1-octyloxycarbonyl)-2,2-dimethylbutyric acid.

Provenance & Evidence